Water-insoluble azo dyestuffs



Patented Sept. 30, 1941 UNIHTED sTATEs PATENT OFFICE Werner Zerweck andWalter Brunner, Frankfort-on-the-Main-Fechenheim, Germany, assignors toGeneral Aniline & Film Corporation, New York, N. Y., a corporation ofDelaware No Drawing. Application April 4, 1940, Serial No. 327,830. InGermany April 14, 1939' solution, containing per liter the diazocompound j 4 Claims.

Our present invention relates to waterinsoluble azo-dyestufis moreparticularly to those of the general formula:

c O-NHQ-hal OOHz wherein R stands for a member of the group consistingof phenyl and chlorophenyl and X for a member of the group consisting ofhydrogen and halogen. They are obtained by combining as such or on asubstratum the'diazo'compound of 1-amino-3.5-dimethyl-G-phenoxyberizeneswhich contain in one of the benzene nuclei halogen Well boiled and driedcotton yarn is impregnated with a solution containing per liter 1.8 grs.of 1-(2'.3'-hydroxynaphthoylamino) -2.5-dimethoxy-i-chlorobenzene, 5ccms. of a caustic soda solution of 34 B. and 5 ccms. of Turkey red oiland well centrifugated. Then without being dried the cotton goods istreated with a of 1.4 gr's. of 1-amino-3.5-dimethyl-chloro-6-phenoxy-benzene which has been nearly neutralized by the addition ofsodium acetate then well rinsed-and soaped. v In this manner, on thefiber the dyestufi of the formula:

HaC l N cm III on 0on3 r CONHC 'Cl OOH:

is obtained, which dyes bright and fast red shades.

l-amino-B.5-dimethyl-6-phenoxybenzene is obtainable by. reacting withthe potassium salt of ahead on 1.3-dimethyl 4-chloro-5-nitrobenzene anda subsequent reduction. It boils at 3 mms. at 155 to 1-56". and melts at46. By the action of sulfurylchloride in the' presence ofchlorobenzen'e, advantageously on its acetyl compound, a

chlorine atom is introduced into the' benzene nucleus. The formedhalogeno compound crystallizes from alcohol as colorless needles of 76melting point, the acetyl derivative melts at 143 to 144.

When replacing the aforesaid diazo compound. by the corresponding amountof the diazo compound of 1-amino-3.5-dimethyl-bromo-6-phenoxybenzenelikewise bright red dyeings of good fastness properties are obtained.

The aforesaid bromo compound is obtainable 2. A waterinsolubleazodyestuft of the formula: by the action of bromine in the presence ofglacial acetic acid on 1-amino-3.5-dimethyl-6- V phenoxybenzene oradvantageously its acetyl compound. The bromo compound crystallizes 5from methanol as colorless leafietsof 90 melting point, itsacetyl-derivative melts at 168.

When developing the impregnated cotton goods 7 with a nearly neutralizeddiazo solution of l-ami- HSC no-3.5-dimethyl 4' chlorphenoxybenzene the10 formed dyestufi of the formula:

OH OCH:

OCH;

a: "T 21?" w 'hich dyestufi dyes bright and fast red shades.

3. Awaterinso1u ble azodyestufi of the formula:

Hac-

g gs

CH: N

dyes brightand fastscarlet-red shades! .i'Iheaforesaid.1-amino-3.5sdimethyl4 chloro- OH OCH: phenoxy benzene, whichboils'i at -3 mm'sfat 168 is obtainable by acting with the potassiumsalt CONH Br of 4-ch1orophenol on 1.3-dimethy1e4-chloro-5- nitrobenzeneand reducing the condensation 00m product with iron in the presence ofacetic acid. 40 which d t fi dyes bright and f td shades We claim: 4 1.Waterinsoluble azodyestufis of the formula! A watergllsoluble azodyesmfiof the formula" R f A HzC l I. l

on can. w

0.0m. OCH I I whereinR stands fora member-"of the group con- 6o I 3 p IOH sisting ofphenyl and chlorophenyl and ior j .v a m of t r uconsisting of hydr g which dyestufi dyes bright and. fast scarlet. redand halogen," which-dyestufis are'difstiriguished h 5 byaremarkablebeauty of shades and-goodiast 1 r WERNER ZERWEGK.

" I "WALTER BRUNNEB.-

ness properties.

